Efficient access
to chiral cyclopentadienyl esters from readily accessible chiral enynyl
ester substrates is developed. Typically high levels of chirality
transfer realized in this homogeneous gold catalysis are attributed
to the intermediacy of a chiral bent allene gold complex. Cyclopentadienyl
esters can be prepared in good yields and with excellent enantiomeric
excesses. The synthetic utilities of the chiral cyclopentadienyl esters
are demonstrated by the Diels–Alder reactions, fluorination,
alkylation, and epoxidation without any notable erosion of enantiopurity.